organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Amiloride hydro­chloride methanol disolvate

aInstitut für Organische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany, and bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 11 May 2010; accepted 12 May 2010; online 15 May 2010)

In the crystal of the title compound [systematic name: 2-(3,5-diamino-6-chloro­pyrazin-2-ylcarbon­yl)guanidinium chloride methanol disolvate], C6H9ClN7O+·Cl·2CH3OH , the components are connected by N—H⋯N, N—H⋯Cl, N—H⋯O, O—H⋯Cl and O—H⋯O hydrogen bonds into a three-dimensional network. The dihedral angle between the aromatic ring and the guanidine residue is 6.0 (2)°.

Related literature

For other salts of amiloride, see: Pretscher et al. (2001[Pretscher, A., Brisander, M., Bauer-Brandl, A. & Hansen, L. K. (2001). Acta Cryst. C57, 1217-1219.]); Zeslawska et al. (2004[Zeslawska, E., Oleksyn, B. & Stadnicka, K. (2004). Struct. Chem. 15, 567-571.]).

[Scheme 1]

Experimental

Crystal data
  • C6H9ClN7O+·Cl·2CH4O

  • Mr = 330.19

  • Monoclinic, P 21 /n

  • a = 5.9473 (5) Å

  • b = 16.7278 (17) Å

  • c = 14.7784 (15) Å

  • β = 90.080 (8)°

  • V = 1470.2 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.46 mm−1

  • T = 173 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Stoe IPDS II two-circle diffractometer

  • Absorption correction: multi-scan (MULABS; Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.874, Tmax = 0.914

  • 19184 measured reflections

  • 2739 independent reflections

  • 1852 reflections with I > 2σ(I)

  • Rint = 0.071

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.080

  • S = 0.96

  • 2739 reflections

  • 212 parameters

  • 9 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N31—H31A⋯N4i 0.88 (1) 2.14 (1) 2.996 (3) 165 (3)
N31—H31B⋯Cl1ii 0.87 (1) 2.50 (2) 3.281 (3) 150 (3)
N51—H51A⋯Cl1iii 0.88 (1) 2.54 (1) 3.396 (3) 165 (3)
N51—H51B⋯O11 0.88 (1) 2.11 (2) 2.781 (3) 133 (3)
N12—H12⋯O2Miv 0.87 (1) 2.14 (2) 2.912 (3) 149 (3)
N14—H14A⋯Cl1v 0.88 (1) 2.34 (1) 3.188 (3) 162 (3)
N14—H14B⋯O2Miv 0.88 (1) 1.93 (2) 2.783 (3) 162 (3)
N15—H15A⋯Cl1v 0.88 (1) 2.61 (2) 3.367 (3) 145 (3)
N15—H15B⋯O11 0.88 (1) 2.03 (3) 2.688 (3) 131 (3)
O1M—H1M⋯Cl1 0.84 2.26 3.091 (2) 171
O2M—H2M⋯O1M 0.84 1.91 2.745 (3) 170
Symmetry codes: (i) -x+2, -y, -z+1; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (v) x-1, y, z.

Data collection: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Related literature top

For other pseudopolymorphs of amiloride, see: Pretscher et al. (2001); Zeslawska et al. (2004).

Experimental top

Crystals of the title structure were obtained by recrystallization of amiloride hydrochloride (100 mg) from a methanol (3 g) solution.

Refinement top

H atoms bonded to O and C were geometrically positioned and refined using a riding model with fixed individual displacement parameters [U(H) = 1.5 Ueq(C,O)] using a riding model with C—H = 0.98Å and O—H = 0.84 Å, respectively. The methyl and hydroxyl groups were allowed to rotate but not to tip. H atoms bonded to N were refined with a distance restraint of 0.88 (1)Å and with U(H) = 1.2 Ueq(N).

Structure description top

For other pseudopolymorphs of amiloride, see: Pretscher et al. (2001); Zeslawska et al. (2004).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Perspective view of the asymmetric unit of the title compound. Displacement ellipsoids are at the 50° probability level.
2-(3,5-diamino-6-chloropyrazin-2-ylcarbonyl)guanidinium chloride methanol disolvate top
Crystal data top
C6H9ClN7O+·Cl·2CH4OF(000) = 688
Mr = 330.19Dx = 1.492 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 11166 reflections
a = 5.9473 (5) Åθ = 3.7–25.7°
b = 16.7278 (17) ŵ = 0.46 mm1
c = 14.7784 (15) ÅT = 173 K
β = 90.080 (8)°Block, colourless
V = 1470.2 (2) Å30.30 × 0.25 × 0.20 mm
Z = 4
Data collection top
Stoe IPDS II two-circle
diffractometer
2739 independent reflections
Radiation source: fine-focus sealed tube1852 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.071
ω scansθmax = 25.6°, θmin = 3.6°
Absorption correction: multi-scan
(MULABS; Spek, 2009; Blessing, 1995)
h = 77
Tmin = 0.874, Tmax = 0.914k = 2020
19184 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 0.96 w = 1/[σ2(Fo2) + (0.0253P)2]
where P = (Fo2 + 2Fc2)/3
2739 reflections(Δ/σ)max < 0.001
212 parametersΔρmax = 0.22 e Å3
9 restraintsΔρmin = 0.25 e Å3
Crystal data top
C6H9ClN7O+·Cl·2CH4OV = 1470.2 (2) Å3
Mr = 330.19Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.9473 (5) ŵ = 0.46 mm1
b = 16.7278 (17) ÅT = 173 K
c = 14.7784 (15) Å0.30 × 0.25 × 0.20 mm
β = 90.080 (8)°
Data collection top
Stoe IPDS II two-circle
diffractometer
2739 independent reflections
Absorption correction: multi-scan
(MULABS; Spek, 2009; Blessing, 1995)
1852 reflections with I > 2σ(I)
Tmin = 0.874, Tmax = 0.914Rint = 0.071
19184 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0509 restraints
wR(F2) = 0.080H atoms treated by a mixture of independent and constrained refinement
S = 0.96Δρmax = 0.22 e Å3
2739 reflectionsΔρmin = 0.25 e Å3
212 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.4136 (4)0.07364 (14)0.32999 (16)0.0187 (6)
C20.5851 (5)0.02607 (17)0.32413 (18)0.0179 (6)
Cl20.62266 (14)0.02883 (5)0.22493 (5)0.0315 (2)
C30.7485 (5)0.01732 (16)0.39568 (19)0.0182 (6)
N310.9232 (4)0.03176 (16)0.38692 (17)0.0241 (6)
H31A1.006 (5)0.0400 (18)0.4354 (14)0.029*
H31B0.939 (5)0.0621 (16)0.3394 (14)0.029*
N40.7256 (4)0.06106 (13)0.47133 (16)0.0179 (5)
C50.5473 (5)0.11111 (16)0.47856 (19)0.0173 (6)
N510.5303 (5)0.15414 (15)0.55477 (18)0.0256 (6)
H51A0.624 (4)0.1497 (18)0.6007 (15)0.031*
H51B0.410 (3)0.1839 (16)0.561 (2)0.031*
C60.3874 (5)0.11725 (17)0.40695 (19)0.0168 (6)
C110.1930 (5)0.17089 (18)0.4093 (2)0.0202 (7)
O110.1433 (4)0.21444 (12)0.47391 (14)0.0249 (5)
N120.0642 (4)0.16832 (14)0.33015 (15)0.0173 (5)
H120.110 (5)0.1370 (14)0.2874 (15)0.021*
C130.1158 (5)0.21632 (17)0.3097 (2)0.0196 (7)
N140.2054 (4)0.20867 (16)0.22820 (18)0.0250 (6)
H14A0.326 (3)0.2377 (16)0.218 (2)0.030*
H14B0.134 (5)0.1739 (15)0.1935 (18)0.030*
N150.1985 (4)0.26602 (16)0.37008 (18)0.0250 (6)
H15A0.310 (4)0.2979 (16)0.355 (2)0.030*
H15B0.141 (5)0.2664 (19)0.4246 (11)0.030*
Cl10.36907 (12)0.32420 (4)0.23835 (5)0.02329 (18)
O1M0.4195 (4)0.44145 (13)0.39875 (15)0.0335 (6)
H1M0.40010.41390.35190.050*
C1M0.2507 (6)0.4216 (2)0.4641 (2)0.0355 (8)
H1M10.26370.36500.48020.053*
H1M20.10150.43180.43840.053*
H1M30.27160.45450.51830.053*
O2M0.4108 (4)0.59993 (13)0.35076 (15)0.0315 (6)
H2M0.41960.55040.35920.047*
C2MA0.2302 (6)0.6318 (2)0.4037 (2)0.0370 (9)
H2M10.08830.60710.38480.056*
H2M20.22140.68980.39450.056*
H2M30.25730.62050.46780.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0148 (14)0.0184 (13)0.0229 (14)0.0003 (11)0.0025 (10)0.0018 (11)
C20.0171 (15)0.0209 (15)0.0157 (14)0.0018 (13)0.0030 (12)0.0000 (12)
Cl20.0278 (5)0.0391 (5)0.0276 (4)0.0122 (4)0.0061 (3)0.0114 (4)
C30.0142 (15)0.0149 (15)0.0254 (16)0.0011 (13)0.0002 (12)0.0037 (13)
N310.0209 (14)0.0244 (15)0.0268 (15)0.0082 (12)0.0059 (12)0.0050 (12)
N40.0133 (13)0.0146 (12)0.0258 (14)0.0018 (10)0.0036 (10)0.0012 (10)
C50.0172 (16)0.0129 (14)0.0220 (16)0.0037 (12)0.0017 (12)0.0012 (12)
N510.0250 (16)0.0269 (15)0.0250 (15)0.0067 (12)0.0070 (12)0.0061 (12)
C60.0125 (15)0.0141 (14)0.0238 (16)0.0012 (12)0.0014 (12)0.0002 (12)
C110.0186 (16)0.0162 (15)0.0257 (16)0.0046 (13)0.0006 (13)0.0037 (14)
O110.0265 (12)0.0212 (11)0.0268 (12)0.0062 (9)0.0021 (9)0.0042 (9)
N120.0174 (13)0.0166 (13)0.0180 (13)0.0043 (11)0.0024 (10)0.0011 (10)
C130.0141 (15)0.0156 (15)0.0290 (17)0.0004 (12)0.0001 (13)0.0027 (13)
N140.0197 (15)0.0272 (15)0.0280 (16)0.0083 (11)0.0061 (12)0.0000 (12)
N150.0197 (15)0.0263 (15)0.0290 (15)0.0103 (12)0.0039 (12)0.0018 (12)
Cl10.0196 (4)0.0206 (4)0.0296 (4)0.0024 (3)0.0022 (3)0.0006 (3)
O1M0.0372 (14)0.0317 (14)0.0317 (13)0.0091 (11)0.0034 (11)0.0026 (10)
C1M0.040 (2)0.0347 (19)0.0318 (19)0.0092 (17)0.0015 (16)0.0054 (16)
O2M0.0344 (14)0.0271 (13)0.0328 (13)0.0055 (11)0.0006 (11)0.0064 (11)
C2MA0.039 (2)0.033 (2)0.039 (2)0.0027 (17)0.0032 (17)0.0001 (16)
Geometric parameters (Å, º) top
N1—C21.297 (4)N12—H120.866 (10)
N1—C61.360 (4)C13—N151.316 (4)
C2—C31.443 (4)C13—N141.322 (4)
C2—Cl21.745 (3)N14—H14A0.880 (10)
C3—N311.331 (4)N14—H14B0.884 (10)
C3—N41.343 (4)N15—H15A0.880 (10)
N31—H31A0.880 (10)N15—H15B0.876 (10)
N31—H31B0.872 (10)O1M—C1M1.432 (4)
N4—C51.355 (4)O1M—H1M0.8400
C5—N511.341 (4)C1M—H1M10.9800
C5—C61.426 (4)C1M—H1M20.9800
N51—H51A0.879 (10)C1M—H1M30.9800
N51—H51B0.878 (10)O2M—C2MA1.433 (4)
C6—C111.464 (4)O2M—H2M0.8400
C11—O111.238 (3)C2MA—H2M10.9800
C11—N121.398 (4)C2MA—H2M20.9800
N12—C131.371 (4)C2MA—H2M30.9800
C2—N1—C6118.4 (2)C11—N12—H12117 (2)
N1—C2—C3122.9 (3)N15—C13—N14121.9 (3)
N1—C2—Cl2118.7 (2)N15—C13—N12120.8 (3)
C3—C2—Cl2118.4 (2)N14—C13—N12117.2 (3)
N31—C3—N4119.8 (3)C13—N14—H14A116 (2)
N31—C3—C2121.1 (3)C13—N14—H14B114 (2)
N4—C3—C2119.1 (3)H14A—N14—H14B131 (3)
C3—N31—H31A117 (2)C13—N15—H15A119 (2)
C3—N31—H31B122 (2)C13—N15—H15B119 (2)
H31A—N31—H31B120 (3)H15A—N15—H15B122 (3)
C3—N4—C5118.8 (2)C1M—O1M—H1M109.5
N51—C5—N4117.2 (3)O1M—C1M—H1M1109.5
N51—C5—C6122.3 (3)O1M—C1M—H1M2109.5
N4—C5—C6120.5 (3)H1M1—C1M—H1M2109.5
C5—N51—H51A124 (2)O1M—C1M—H1M3109.5
C5—N51—H51B117 (2)H1M1—C1M—H1M3109.5
H51A—N51—H51B119 (3)H1M2—C1M—H1M3109.5
N1—C6—C5120.3 (3)C2MA—O2M—H2M109.5
N1—C6—C11116.1 (2)O2M—C2MA—H2M1109.5
C5—C6—C11123.6 (3)O2M—C2MA—H2M2109.5
O11—C11—N12122.2 (3)H2M1—C2MA—H2M2109.5
O11—C11—C6124.6 (3)O2M—C2MA—H2M3109.5
N12—C11—C6113.2 (3)H2M1—C2MA—H2M3109.5
C13—N12—C11126.4 (2)H2M2—C2MA—H2M3109.5
C13—N12—H12116 (2)
C6—N1—C2—C30.1 (4)N51—C5—C6—N1178.7 (3)
C6—N1—C2—Cl2178.9 (2)N4—C5—C6—N10.8 (4)
N1—C2—C3—N31179.6 (3)N51—C5—C6—C110.6 (4)
Cl2—C2—C3—N310.5 (4)N4—C5—C6—C11178.9 (3)
N1—C2—C3—N41.1 (4)N1—C6—C11—O11179.6 (3)
Cl2—C2—C3—N4178.0 (2)C5—C6—C11—O112.2 (4)
N31—C3—N4—C5179.5 (3)N1—C6—C11—N120.1 (4)
C2—C3—N4—C51.1 (4)C5—C6—C11—N12178.1 (3)
C3—N4—C5—N51179.7 (2)O11—C11—N12—C136.0 (4)
C3—N4—C5—C60.2 (4)C6—C11—N12—C13174.3 (3)
C2—N1—C6—C50.8 (4)C11—N12—C13—N156.9 (4)
C2—N1—C6—C11179.0 (3)C11—N12—C13—N14175.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N31—H31A···N4i0.88 (1)2.14 (1)2.996 (3)165 (3)
N31—H31B···Cl1ii0.87 (1)2.50 (2)3.281 (3)150 (3)
N51—H51A···Cl1iii0.88 (1)2.54 (1)3.396 (3)165 (3)
N51—H51B···O110.88 (1)2.11 (2)2.781 (3)133 (3)
N12—H12···O2Miv0.87 (1)2.14 (2)2.912 (3)149 (3)
N14—H14A···Cl1v0.88 (1)2.34 (1)3.188 (3)162 (3)
N14—H14B···O2Miv0.88 (1)1.93 (2)2.783 (3)162 (3)
N15—H15A···Cl1v0.88 (1)2.61 (2)3.367 (3)145 (3)
N15—H15B···O110.88 (1)2.03 (3)2.688 (3)131 (3)
O1M—H1M···Cl10.842.263.091 (2)171
O2M—H2M···O1M0.841.912.745 (3)170
Symmetry codes: (i) x+2, y, z+1; (ii) x+3/2, y1/2, z+1/2; (iii) x+1/2, y+1/2, z+1/2; (iv) x+1/2, y1/2, z+1/2; (v) x1, y, z.

Experimental details

Crystal data
Chemical formulaC6H9ClN7O+·Cl·2CH4O
Mr330.19
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)5.9473 (5), 16.7278 (17), 14.7784 (15)
β (°) 90.080 (8)
V3)1470.2 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.46
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerStoe IPDS II two-circle
Absorption correctionMulti-scan
(MULABS; Spek, 2009; Blessing, 1995)
Tmin, Tmax0.874, 0.914
No. of measured, independent and
observed [I > 2σ(I)] reflections
19184, 2739, 1852
Rint0.071
(sin θ/λ)max1)0.608
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.080, 0.96
No. of reflections2739
No. of parameters212
No. of restraints9
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.25

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N31—H31A···N4i0.880 (10)2.137 (13)2.996 (3)165 (3)
N31—H31B···Cl1ii0.872 (10)2.497 (18)3.281 (3)150 (3)
N51—H51A···Cl1iii0.879 (10)2.540 (13)3.396 (3)165 (3)
N51—H51B···O110.878 (10)2.11 (2)2.781 (3)133 (3)
N12—H12···O2Miv0.866 (10)2.137 (18)2.912 (3)149 (3)
N14—H14A···Cl1v0.880 (10)2.341 (14)3.188 (3)162 (3)
N14—H14B···O2Miv0.884 (10)1.930 (15)2.783 (3)162 (3)
N15—H15A···Cl1v0.880 (10)2.61 (2)3.367 (3)145 (3)
N15—H15B···O110.876 (10)2.03 (3)2.688 (3)131 (3)
O1M—H1M···Cl10.842.263.091 (2)171.3
O2M—H2M···O1M0.841.912.745 (3)170.1
Symmetry codes: (i) x+2, y, z+1; (ii) x+3/2, y1/2, z+1/2; (iii) x+1/2, y+1/2, z+1/2; (iv) x+1/2, y1/2, z+1/2; (v) x1, y, z.
 

References

First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–38.  CrossRef CAS Web of Science IUCr Journals Google Scholar
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